Shortly after Larry Ellison, the billionaire CEO of Oracle Corp. and owner of the BMW Oracle Racing Team, won the 33rd America's Cup off the coast of Valencia, Spain, in February 2010, a reception was held in his honor in the rotunda at San Francisco City Hall.

The event drew members of Ellison's sailing crew, business and political heavyweights such as former Secretary of State George Schultz, and other VIPs. Attendees posed for photographs with the tall, glittering silver trophy at the base of the grand staircase.

As part of the celebration, Ellison helped Mayor Gavin Newsom into an official BMW Oracle Racing Team jacket, and Newsom granted Ellison a key to the city, a symbolic honor usually reserved for heads of state and the San Francisco Giants after they won the World Series. Shortly after, the mayor and the guest of honor, whom Forbes magazine ranked as the sixth-richest person in the world, sat down for a face-to-face.

That meeting marked the beginning of the city's bid to host the 34th America's Cup in San Francisco in 2013. Since securing the Cup, Ellison has made no secret of his desire to stage the 159-year-old sailing match against the iconic backdrop of the San Francisco Bay, a natural amphitheater that could be ringed with spectators gathered ashore while media images of the stunningly expensive yachts are broadcast internationally.

Newsom and other elected officials have feverishly championed the idea, touting it as an opportunity for a boost to the region's anemic economy. The city's Budget & Legislative Analyst projects roughly $1.2 billion in economic activity associated with the event — the real prize, as far as business interests are concerned. It would also create the equivalent of 8,840 jobs, mostly in the form of overtime for city workers and short-term gigs for the private sector.

While the idea has won preliminary support from most members of the Board of Supervisors, serious questions are beginning to arise as the finer details of the agreement emerge and the date for a final decision draws near.

Ellison and the race organizers would be granted control of 35 acres of prime waterfront property in exchange for selecting San Francisco as the venue for the Cup and investing $150 million into Port of San Francisco infrastructure. But the event would result in a negative net impact to city coffers.

Hosting the event and meeting Ellison's demands for property would cost the city about $128 million, according the Budget & Legislative Analyst, just as city leaders grapple with closing a projected $712 million deficit in the budget cycle spanning 2011 and 2012.

Part of the impact is an estimated $86 million in lost revenue associated with rent-free leases the city would enter into with Ellison's LLC, the America's Cup Event Authority (ACEA). In exchange for selecting San Francisco as a venue and investing in port infrastructure, ACEA would win long-term control of Piers 30-32, Pier 50, and Seawall Lot 330 — waterfront real estate owned by the Port of San Francisco, with development rights included. Seawall Lot 330, a 2.5-acre triangular parcel bordered by the Embarcadero at the base of Bryant Street, would either be leased long-term or transferred outright to ACEA.

The most vociferous opponent of the America's Cup plan is Sup. Chris Daly, who has voiced scathing criticism of the notion that the city would subsidize a billionaire's yacht race at a time of fiscal instability. "The question is whether or not the package that San Francisco's putting together is good or bad for the city," Daly told the Guardian, "and whether or not it's the best deal the city can get."